(1) The users will be able to understand the logical distinction between Outlook (the client) and Exchange (the server). They will see that they can use that same client to manage multiple email accounts.
(2) The users will be able to manage their own mail from their old, Express Mail accounts.
(3) As these users will be going through a series of changes with regard to communications in the next year or two, it would be better for each change to be perceived as a small step. Understanding Outlook and getting used to it may be the biggest single change. So that should happen asap.
The above is certainly true for PC users. Mac users should perhaps wait til the real Outlook for Mac comes out so they don't have to learn Entourage as an intermediate step.
This first video gives a very quick overview of Outlook. Note that at the end of the video there is a brief demo of making a contact. Contacts in Outlook will become important in the future when we go to unified communications, as that is how people will place their phone calls. Also contacts is how people will manage access to ancillary related services, e.g., calendar sharing or file sharing. It may be that for the latter users before to manage this via a Web browser. But they should be aware that they can manage Contacts from Outlook as well.
The second video is about having multiple email accounts and managing them all from Outlook. There are several reasons to have multiple accounts. Our undergraduate students will have outsourced email, from Google or Microsoft or both. For interacting with these students faculty and staff likely will have accounts in these environments as well. Similarly, for interaction with colleagues on other campuses, one might very well want to use another account, e.g., to use Google Docs or Google Wave. And then one might want to have a personal account that is nonetheless accessible from Outlook.
The third video is about moving mail, from one account to another or from an account to an archive. This video should be useful both for those users who have to move off Express Mail and for those trying to determine the appropriate size quota for users when they do move to the Campus Exchange Server. One thing that is not shown in the video that needs to be considered is how long it takes to move mail when instead of just a few messages without attachments, we're moving a hundred megabytes or more of mail, possibly with quite large file attachments. Conceptually there is no difference in moving large amounts of mail like that, but the that does take time and my experience is that when doing so the computer is not very useful for doing other functions. So there is some inconvenience. Likewise if there is a very large email archive residing on your desktop, sometimes that gets clunky to manipulate.
Finally, when users understand they can move email messages from here to there, it is an opportunity to give some straightforward advice about security and for taking sensible steps to help maintain confidentiality in communication, when necessary. Security isn't a binary state - secure or not. There is less secure and more secure. Not communicating confidential information by email is more secure. Deleting that information after it has been communicated is next. Keeping it on your local machine and not on the server comes after that. Keeping it on the Campus server is better than keeping it on an external host. Confidential information really should never find its way onto an external host. A significant reason why the Campus will continue to provide email service is for that reason. People should understand that.